trimethylsilyl 2,3,4-triacetyl-1β-glucuronic acid methyl ester | 92420-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trimethylsilyl 2,3,4-triacetyl-1β-glucuronic acid methyl ester
• 英文别名: I(2)-D-Glucopyranuronic acid, 1-O-(trimethylsilyl)-, methyl ester, triacetate；methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-trimethylsilyloxyoxane-2-carboxylate
• CAS: 92420-90-1
• 化学式: C₁₆H₂₆O₁₀Si
• 分子量: 406.462
• InChiKey: OUTDBJQMGFFQEI-IPVBOJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  trimethylsilyl 2,3,4-triacetyl-1β-glucuronic acid methyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl (methoxymethyl 2,3,4-tri-O-acetyl-α-D-glucopyranosid)uronate
  参考文献：
  名称：

  立体选择性合成（1-烷氧基烷基）α-和β-d-吡喃葡萄糖苷硬脂酸酯（缩醛-吡喃葡萄糖苷硬脂酸酯）：一种用于治疗癌症的特定细胞抑制剂的新方法

  摘要：

  摘要2,3,4,6-四-O-乙酰基-1-O-三甲基甲硅烷基-β-（5）和-α-d-吡喃葡萄糖醛酸酯（6）与甲醛的二甲基或二乙基缩醛反应，在-78°催化量的三甲基甲硅烷基三氟甲磺酸酯存在下，通过溴乙醛，丙醛，3-苄氧基丙醛，5-羧基戊醛和2-溴己醛制得相应的（1-烷氧基烷基）α-和β-糖苷（缩醛-吡喃葡萄糖基葡糖醛酸酯） C-1构型的产率为41-91％。代替二烷基缩醛，可以使用相应的醛和烷基三甲基甲硅烷基醚。脱乙酰化以良好的产率得到了相应的（缩醛-β-和-α-d-吡喃葡萄糖苷）尿酸甲酯。

  DOI：

  10.1016/0008-6215(88)80082-x
• 作为产物：
  描述：

  苄基beta-D-吡喃葡糖苷酸甲酯三乙酸酯 在 Lindlar's catalyst 吡啶 、 氢气 、 六甲基二硅氮烷 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 trimethylsilyl 2,3,4-triacetyl-1β-glucuronic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 1-O-trimethylsilyl-α- and -β-d-glucopyranuronate

  摘要：

  DOI：

  10.1016/s0008-6215(00)90402-6

文献信息

• Aldosterone Glucuronide, an Important Biomarker: Synthesis and Structure Elucidation of Novel Isomers
  作者：Somraj Guha、Soundararasu Senthilkumar、Edgar Voß、Lutz F. Tietze

  DOI：10.1002/chem.202004154

  日期：2020.12

  diacetate 11 in the presence of TMSOTf gave the 18‐α‐glucuronide 9 a. The 18‐β‐glucuronide 15 b and the 20‐β‐glucuronide 16 b could be obtained by reaction of methyl 2,3,4‐tri‐O‐isobutyryl‐1α‐glucuronate trichloroacetimidate 14 and aldosterone 21‐acetate 8 in the presence of TMSOTf or BF3⋅OEt2. Finally, reaction of aldosterone 21‐acetate 8 and methyl 2,3,4‐triacetyl‐1α‐glucuronate trichloroacetimidate

  醛固酮1是盐皮质激素，它对血压有很大的影响，其葡糖醛酸苷是检测多种疾病的重要标志。在这里，我们描述了不同醛固酮18和20葡糖醛酸内酯的化学合成。在TMSOTf存在下，三甲基甲硅烷基2,3,4-三乙酰基-1-β-葡萄糖醛酸甲酯5b与醛固酮二乙酸酯11的反应得到18-α-葡萄糖醛酸9a。18-β葡萄糖醛酸苷15b中与20-β葡萄糖醛酸苷16b中可以通过甲基的反应而获得2,3,4-三ö异丁酰基1α葡糖醛三氯14和醛固酮21-乙酸酯8在将TMSOTf或BF的存在3 ⋅OEt 2。最后，在TMSOTf存在下，醛固酮21-乙酸8与2,3,4-三乙酰基-1α-葡萄糖醛酸三氯乙酰胺酸甲酯19反应，得到相应的18-β-三乙酰基葡萄糖醛酸甲酯9 b，然后将其转化为所需的醛固酮18 -β-葡萄糖醛酸3通过两个酶促转化。
• A novel method for stereoselective glucuronidation
  作者：Bilha Fischer、Abraham Nudelman、Margareta Ruse、Jacob Herzig、Hugo E. Gottlieb、Ehud Keinan

  DOI：10.1021/jo00199a046

  日期：1984.12
• Intensely Cytotoxic Anthracycline Prodrugs:  Glucuronides
  作者：Elena Bakina、Zheng Wu、Michael Rosenblum、David Farquhar

  DOI：10.1021/jm970066d

  日期：1997.12.1

  We previously reported the synthesis of a series of doxorubicin analogue prodrugs that give rise to intensely cytotoxic metabolites in the presence of carboxylate esterases. We now report studies on structurally related beta-glucuronide prodrugs that are converted to similar potent metabolites in the presence of beta-glucuronidases. These prodrugs were prepared by reductive condensation of daunomycin or doxorubicin with methyl 1-O-[(1'RS)-1'-ethoxy-4'-oxobutyl]-2,3,4-tri-O-acetyl-beta-D-glucopyranosyluronate in the presence of sodium cyanoborohydride followed by base-mediated cleavage of the glucuronate protective groups. The doxorubicin derivatives were isolated in very low yield, most likely because of the inherent base lability of the parent aglycone. By contrast, fairly good yields of the more base-stable daunomycin analogues were obtained. The target daunomycin glucuronide, N-[(4''RS)-4''-ethoxy -4''-(sodium 1'''-O-beta-D-glucopyranuronate)butyl]daunorubicin (6a), bad a half-life of 30 h when incubated at a concentration of 12 mu M in aqueous 0.05 M phosphate buffer, pH 7.4, at 37 degrees C. Under identical conditions in the presence of 197 units/mu mol of Escherichia coli beta-glucuronidase, 6a was hydrolyzed with a half-life of 1.7 h. The single metabolite observed was chromatographically identical with that formed from the hydrolysis of N-(4,4-diacetoxybut-1-yl)daunomycin by carboxylate esterases. 6a was approximately 10000-fold more toxic to human A375 melanoma cells in the presence of E. coli beta-glucuronidase than in the absence of the enzyme. These findings indicate the therapeutic potential of anthracycline glucuronide prodrugs as independent entities or for use in conjunction with enzyme tissue-targeting strategies such as antibody-directed enzyme prodrug therapy (ADEPT) or gene-directed enzyme prodrug therapy (GDEPT).
• TIETZE, LUTZ F.;SEELE, RAINER;LEITING, BARBARA;KRACH, THOMAS, CARBOHYDR. RES., 180,(1988) N 2, C. 253-262
  作者：TIETZE, LUTZ F.、SEELE, RAINER、LEITING, BARBARA、KRACH, THOMAS

  DOI：——

  日期：——